[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[CH:2]=1.[N:12]([O-])=O.[Na+].O.O.[Cl:18][Sn]Cl>Cl>[ClH:18].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][NH2:12])[CH:2]=1To a solution of quinolin-3-ylamine (5 g, 35 mmol) in conc. HCl (12 mL) was added dropwise an aqueous solution (4 mL) of NaNO2 (2.42 g, 35 mmol) at 0° C. The resulting mixture was stirred for 1 h, and then treated with a solution of SnCl2.2H2O (15.8 g, 70 mmol) in conc. HCl (15 mL). The reaction solution was stirred for an additional 2 h at RT. The precipitate was filtered and washed with EtOH and ether to yield 1-(quinolin-3-yl)hydrazine hydrochloride (4.5 g, 81% yield), which was used in the next reaction without further purification.
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